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Brønsted Acid-Promoted Olefin Aziridination and Formal anti-Aminohydroxylation

Joseph M. Mahoney, Colin R. Smith and Jeffrey N. Johnston*

*Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, Email:

J. M. Mahoney, C. R. Smith, J. N. Johnston, J. Am. Chem. Soc., 2005, 127, 1354-1355.

DOI: 10.1021/ja045608c


A straightforward synthesis of aziridines is reported from electron-rich azides, electron-deficient olefins, and triflic acid in cold acetonitrile. Ester substrates bearing a nucleophilic carbonyl give products of an olefin aminohydroxylation.

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ID: J48-Y2005-2220